Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 17:32:58 UTC |
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Updated at | 2021-06-29 23:50:21 UTC |
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NP-MRD ID | NP0025415 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Citrifolinin A, Dehydromethoxygaertneroside |
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Provided By | JEOL Database |
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Description | Methyl (1S,4aS,7R,7aS)-4'-(4-hydroxy-3-methoxybenzoyl)-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Citrifolinin A, Dehydromethoxygaertneroside is found in Morinda citrifolia L. and Morinda morindoides. It was first documented in 2001 (Sang, S., et al.). Based on a literature review very few articles have been published on methyl (1S,4aS,7R,7aS)-4'-(4-hydroxy-3-methoxybenzoyl)-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate. |
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Structure | [H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])C(=O)C1=C([H])[C@]2(OC1=O)C([H])=C([H])[C@]1([H])C(=C([H])O[C@@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])[C@]21[H])C(=O)OC([H])([H])[H] InChI=1S/C27H28O14/c1-36-16-7-11(3-4-15(16)29)19(30)13-8-27(41-24(13)35)6-5-12-14(23(34)37-2)10-38-25(18(12)27)40-26-22(33)21(32)20(31)17(9-28)39-26/h3-8,10,12,17-18,20-22,25-26,28-29,31-33H,9H2,1-2H3/t12-,17-,18-,20-,21+,22-,25+,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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Methyl (1S,4as,7R,7as)-4'-(4-hydroxy-3-methoxybenzoyl)-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid | Generator |
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Chemical Formula | C27H28O14 |
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Average Mass | 576.5070 Da |
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Monoisotopic Mass | 576.14791 Da |
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IUPAC Name | methyl (1S,4aS,7R,7aS)-4'-(4-hydroxy-3-methoxybenzoyl)-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate |
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Traditional Name | methyl (1S,4aS,7R,7aS)-4'-(4-hydroxy-3-methoxybenzoyl)-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])C(=O)C1=C([H])[C@]2(OC1=O)C([H])=C([H])[C@]1([H])C(=C([H])O[C@@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])[C@]21[H])C(=O)OC([H])([H])[H] |
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InChI Identifier | InChI=1S/C27H28O14/c1-36-16-7-11(3-4-15(16)29)19(30)13-8-27(41-24(13)35)6-5-12-14(23(34)37-2)10-38-25(18(12)27)40-26-22(33)21(32)20(31)17(9-28)39-26/h3-8,10,12,17-18,20-22,25-26,28-29,31-33H,9H2,1-2H3/t12-,17-,18-,20-,21+,22-,25+,26+,27-/m1/s1 |
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InChI Key | RIDIXCFHWOHPTF-SPJPOALZSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Iridoid O-glycosides |
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Alternative Parents | |
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Substituents | - Iridoid o-glycoside
- Terpene lactone
- Hexose monosaccharide
- O-glycosyl compound
- Iridoid-skeleton
- Glycosyl compound
- Monoterpenoid
- Methoxyphenol
- Aromatic monoterpenoid
- Bicyclic monoterpenoid
- Phenoxy compound
- Phenol ether
- Anisole
- Methoxybenzene
- Benzoyl
- Aryl ketone
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Dicarboxylic acid or derivatives
- 2-furanone
- Benzenoid
- Vinylogous ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Dihydrofuran
- Methyl ester
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Polyol
- Ether
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Aldehyde
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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